Copper-Catalyzed Synthesis of Axially Chiral Biaryls with Diaryliodonium Salts as Arylation Reagents
Ji-Wei Zhang,
Shao-Hua Xiang,
Shaoyu Li,
Bin Tan
Affiliations
Ji-Wei Zhang
Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China
Shao-Hua Xiang
Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China
Shaoyu Li
Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China
Bin Tan
Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China
NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [3,3]-sigmatropic rearrangement. This reaction features mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols.
